Thionyl Chloride → 2,5-Dimethoxybenzyl chloride

HRID 1757554Notes

Reaction equation

HRID 1757554 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5]O.S(Cl)([Cl:15])=O>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][Cl:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1184952,5-Dimethoxybenzyl alcohol

Product 1

HCID 2911942,5-Dimethoxybenzyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a nitrogen atmosphere, 2.00 g (11.9 mmol.) of 2,5-dimethoxybenzyl alcohol was dissolved in 10 ml of dichloromethane. The obtained solution was placed in an ice-bath, and to this was dropwise added a solution of 0.87 ml (12.0 mmol.) of thionyl chloride in 2 ml of dichloromethane. The mixture was then stirred at room temperature for 1.5 hour. The mixture wasplaced under reduced pressure at room temperature to distill off the solvent to give 2.22 g of the desired compound as a pale yellow oil.

Workup

  1. customThe obtained solution was placed in an ice-bath
  2. customwasplaced under reduced pressure at room temperature
  3. distillationto distill off the solvent

Sources & evidence

ORD record
ord-968682d7e7b64cd1acb33d013af0633d
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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